Sodium Carbonate → (1SR,3SR)-3-[3-(2-Chloro-6-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

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Reaktionsgleichung

Br[C:2]1[N:6]2[CH:7]=[C:8]([NH:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH:14]([OH:18])[CH2:13]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[C:22]([O:35][CH3:36])[N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[C:24]([C:2]2[N:6]3[CH:7]=[C:8]([NH:11][CH:12]4[CH2:17][CH2:16][CH2:15][CH:14]([OH:18])[CH2:13]4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:23]=[C:22]([O:35][CH3:36])[N:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

To a solution of 3-trans-RS/RS(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol [intermediate J step 2] (1 eq, 10.1 mmol, 3.4 g), 2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.05 eq, 10.1 mmol, 2.9 g), Na2CO3 (2 eq, 19 mmol, 2 g) in dioxane (45 ml) and water (13.5 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 0.96 mmol, 224 mg). The reaction mixture is heated at 95° C. for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc to afford the title compound; [M+H]+=343/345.

Aufarbeitung

extractionextracted with EtOAc
washThe combined organic portions are washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-95a853840a7e4c97a2298ceccd3c9ef0
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08367662B2

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